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Holiday Rentals in Chestertown

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Holiday Rentals in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, 52 reviews
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, 4 reviews
"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"
The price is €1,358
per night
4 Jun - 5 Jun
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, 180 reviews
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, 21 reviews
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, 61 reviews
"We had a great time at this very cute cottage and really appreciated the extra touches of the hosts, who were very helpful. The yard is truly a great place to hangout but there were also lots of places to enjoy close by."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 14 reviews
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
9.6 out of 10, Exceptional, 18 reviews
"Had a nice stay. We would definitalty book again."
Beautiful Luxury waterfront Property,clean,Fully sterilized,Family oriented.
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, 161 reviews
"This had everything we needed and Fells Point is a nice area!"
The price is €203
per night
3 Jun - 4 Jun
'At Fells Point' CitySide - 'Tons better than a hotel!'
Bay View Studio Apartment
10.0 out of 10, Exceptional, 25 reviews
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, 17 reviews
"What a delight to have found this property. Beautiful drive to get to the Eastern Shore. Rock Hall The beautiful place that’s tucked in along the Chesapeake Bay. My fiancé and I needed a much desirable getaway. The bungalow at this property was the perfect place just for us to forget about our worries back home. The owners were kind enough to message us. Let us know if the events that were happening in town but more so anything that was happening on the property they gave us just a heads up as...
The price is €258
per night
2 Jun - 3 Jun
BAYSIDE BUNGALOW
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, 19 reviews
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, 7 reviews
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
10.0 out of 10, Exceptional, 6 reviews
"We had the best time staying at this property. What a location! Gorgeous and private! The boat is stunning, immaculate, and well appointed. The beds are amazing. Brian was a wonderful host and helped us through a minor glitch with the lockbox with dedicated speed. The supplemental information is unparalleled! Stay here!"
The price is €674
per night
3 Jun - 4 Jun
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, 267 reviews
"Everything is perfect over there … The paradise on earth .. Highly recommended "
The Heron's Nest at Atlantic Marina
Milton Manor: W/D, WiFi, Free Street Parking
2.0 out of 10, 2 reviews
"Good day! I want to first start off by saying thank you for allowing us to stay in your place. However, I do have so things I want to bring to you attention before I leave a review. 1) There is only one Tv in thee entire place when there are two rooms. 2) The Tv that is there doesn’t even work. 3) The sink doesn’t drain and had old water sitting in it. So, we had to brush our teeth in the shower. 4) Very noisy area. Cars come by all day and night. The neighbors above are very loud not to mention...
The price is €204
per night
4 Jun - 5 Jun
Milton Manor: W/D, WiFi, Free Street Parking
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, 81 reviews
"421Irie is a great property, well managed and maintained by Liz. It was perfect for a weekend of sailing, golf, family and friends. We hosted a small cookout for eight one night, and the cottage was just right for the group. The kitchen is well stocked, the big grill outside was just fine, and the multiple seating locations were ideal for the various attendees. We would love to stay at the cottage again next time we are in Annapolis"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, 80 reviews
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, 28 reviews
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
10.0 out of 10, Exceptional, 6 reviews
"I couldn’t have found a better place this gave us a great nights rest every night. We had a lot planned and all turned out great. Our first night we didn’t stop to eat so we asked Jimmy where we can go he directed us to a great Chinese restaurant. We were right smack in the middle of all our plans. Friday night An Inner Harbor Dinner Cruise. Saturday night a Kenny Chesney Concert. Sunday a Bowie Baysocks game and Monday on our way home stopped at the B&O Railroad Museum. What a great time thank...
The price is €116
per night
3 Jun - 4 Jun
Cozy and peaceful BASEMENT in a house, close to different restaurants and a park
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Chestertown you may be interested in

Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, 677 reviews
"Breakfast area and food was below expectations"
The price is €129
per night
2 Jun - 3 Jun
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, 273 reviews
"nice hotel. helpful staff. stores and dining are walkable distances."
The price is €110
per night
12 Jun - 13 Jun
Red Roof Inn & Suites Chestertown
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, 1,619 reviews
"We visited Annapolis to attend the graduation ceremony at the USNA and wanted a hotel within walking distance from the Academy and the waterfront. We stayed at the Robert Johnson House (one of three properties comprising the Historic Inns). Check-in is done at a different property (Governor Calvert House) just a short walk away on the same street: State Circle. This is also where valet parking is located. If you have a lot of luggage or just prefer not to lug it from check-in to your hotel, I...
The price is €144
per night
1 Jul - 2 Jul
Historic Inns of Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Chestertown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chestertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as €116 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Chestertown?

Yes, there are holiday rentals in Chestertown close to Crumpton Auction, or you can select a more secluded option if you're looking for a relaxing stay. Chestertown is known for its sporting events and university setting. Make sure you have time to check out the festivals and art during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Chestertown?

Expedia has 30 holiday rentals for your stay in Chestertown.

What can I see and do in Chestertown?

Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Wilmer Park is one spot to enjoy nature. Rolphs Wharf Marina and Crumpton Auction are other places to visit while you're in town.

What are holiday rentals like in Chestertown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestertown. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.

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